1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 13957668, compound

HRID 847451Notes

Reaction equation

HRID 847451 reaction equation
[F:1][C:2]([F:27])([F:26])[C:3]1[NH:4][C:5]([C:22](F)([F:24])[F:23])=[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:7]([CH2:14][CH2:15][CH3:16])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].C1CCN2C(=NCCC2)CC1>C1COCC1>[F:24][CH:22]([F:23])[C:5]1[C:6]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:7]([CH2:14][CH2:15][CH3:16])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:3]([C:2]([F:27])([F:1])[F:26])[N:4]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 13957628HCID 13957628, compound

Product 1

HCID 13957668HCID 13957668, compoundYield 64.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 20.0 g (0.05 mole) of diethyl 2,6-bis(trifluoromethyl)-1,4-dihydro-4-n-propyl-3,5-pyridinedicarboxylate, 7.62 g (0.05 mole) of DBU, and 200 ml of THF is held at reflux for 9 hours, cooled and poured into 500 ml of ice water. The mixture is extracted with ether (2×200 ml). The ether extract is washed with diluted hydrochloric acid, dried (MgSO4), and concentrated to give 12.4 g (64.5%) of the desired product, nD25 1.4436.

Workup

  1. temperatureat reflux for 9 hours
  2. temperaturecooled
  3. extractionThe mixture is extracted with ether (2×200 ml)
  4. extractionThe ether extract
  5. washis washed with diluted hydrochloric acid
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e2408e25a49445a89d8e3c0262104fe0
Source dataset
uspto-grants-1992_08
Patent number
US05142055

Reaction notes

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